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20 Strategic Questions to Ask a Prospect

Romain Eliard
Published on
28/5/2025
Professional asking strategic questions over a coffee meeting

During the discovery phase, the questions you ask can be decisive. 🎯

Experienced salespeople have two main skills:

  • Asking the questions that lead to a sale
  • Asking them at the right moment

In fact, “the art of asking the right questions at the right time” has a name: questiology. It’s an art every salesperson should master.

For example, when facing an objection, the difference is obvious:

  • The beginner’s answer that kills your prospect’s trust:

“Your product doesn’t have the quality our company is looking for.”

→ “Don’t worry, you have nothing to be concerned about on that front.”

  • The expert answer that asks a question:

“Your product doesn’t have the quality our company is looking for.”

→ “That’s a good point—it really depends on how you plan to use it. How are you going to use it?”

💡 Tip: Always ask a question right after saying something that could trigger an objection!

Asking the right questions at the right time helps you uncover your prospect’s needs, their true motivations, their blockers and challenges, and which solutions fit best…

Table of Contents:

  • Why do questions drive sales?
  • 20+ strategic questions in 3 key steps

Every well-asked question gives you valuable information and saves you time because you’ll know if your prospect is qualified, if they’re ready to buy, and what solution to offer them.

Why do questions drive sales?

Questiology has become a weapon in sales. Here are 2 reasons why questions improve your sales technique.

You come across as a consultant

Contrary to what you might think, asking questions gives you a more professional image—as long as the questions are sharp and show your expertise.

You’re no longer the salesperson just trying to hit your numbers, but a consultant who brings valuable knowledge with strategic questions.

Think of the discovery phase as a meeting where both sides evaluate if it’s a good idea to work together. You’re trying to find out if this is as beneficial for your company as it is for your prospect—with no bias.

That’s true professionalism.

Get your mindset ready for negotiations

You amplify your prospect’s buying intent

The real power of questions is getting your prospect to identify their own needs and see the value of your offer.

By asking questions that guide their strategy, you involve your contact in implementing your solution.

Asking questions prevents putting the prospect on the defensive with statements. It’s the best way to include them in the process instead of making them shut down.

That way, prospects take ownership of your proposal and start to want to work with you to achieve the objectives you set out—rather than the other way around.

💡Did you know? The top-performing sales reps ask an average of 32 questions during the qualification interview! (Sales Insight Lab, 2022)

20+ Strategic Questions in 3 Key Steps

Since timing is as important as the questions themselves, these are grouped into three stages: revealing the problem, introducing the solution, and preparing next steps.

Answers to these strategic questions will give you the information you need to speed up your deals.

Questions that reveal the problem

Your prospect’s most painful need is what will determine whether they sign at closing.

Your solution needs to solve one of their main problems. To fully understand it and have arguments that hit home, here are a dozen questions to ask:

  • How did you hear about us?
  • What challenges/problems are you facing?
  • How are you currently dealing with [the problem]?
  • Have the solutions you’ve put in place worked? Which ones work or don’t work?
  • What results would you expect from a new solution?
  • When would you like to achieve those results?
  • Why is this a priority for you? Why now?

This first set of qualifying questions helps you understand if your solution is the right fit for your prospect—or if you’re wasting time and should follow up later.

Brush up on the sales techniques you need to know

Questions that introduce your solution

If your prospect is qualified, it’s time to highlight the advantages of your solution.

By continuing with questions, you show the value of choosing your solution. You push your prospect to realize on their own what it would cost them not to work with you sooner!

Here are questions that let you talk about your solution’s benefits:

  • What do you like about your current system? And what would you change?
  • If you don’t find a solution to [the problem], what will happen to your company?
  • How could this situation affect your teams?
  • How much would you be willing to spend to solve [the problem]?
  • If you found the right solution, what impact would it have on your numbers?
  • What would success look like for you with a new solution?
  • What do you especially like about our product?
  • If we start working together today, what will have changed in 6 months?

You’re paving the way for the negotiation phase: the prospect is telling you how much time and money they’re losing without a solution, and realizing it in the process.

How to handle objections?

Now that you’ve shown the worst-case scenario and how to avoid it, move on to the phase where the prospect pictures themselves with you and your solution.

Questions to prepare next steps

You’ve helped your prospect understand the ins and outs of their issues. If you’ve done it well, they’ll have realized the urgency of their problem and the benefits of your solution.

Now, ask the questions that will help YOU organize the next steps in your sales process:

  • How quickly would you like this problem solved?
  • What are your company’s goals?
  • What’s the main obstacle to those goals?
  • Who makes these kinds of decisions? Who else is involved in choosing a solution?

These questions give you what you need to structure your next discussions and move the sale forward.

And, at every stage, it’s best to schedule the next step before ending the meeting.

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